This story takes place ~6 months after Babysitter.

This story contains consensual oral sex between a male cub(10) and his older female teen babysitter(16), along with brief mentions of rejection, bullying, and some crying. If you do not like or cannot handle these topics, please leave or use your blacklist. It is nobody's responsibility but your own to make sure you don't see things you can't handle.

Valentine

Jenny sat in front of her mirror, smiling as she braided her long blond hair and listened to the music blasting through the little speaker sitting next to her on her desk. It was Friday night, and valentines day on top of it, and she'd gotten a call after school that made her heart race. The single mother up the street that moved in over the summer called to ask if she'd be available to babysit tonight because the normal sitter wasn't available last second, and the 16 year old husky was more than happy to take the job and have some private time with her favorite little squirrel for the first time in months. 
A naughty thought ran through the teen's head as she stood and checked herself out in the mirror, quickly pulling off her shirt and pulling on her black zip-up hoodie. Her heart raced slightly as she zipped it up and smiled to herself while she grabbed her things and got ready to leave for the night. She stopped and took one last look at herself, slowly unzipping her jacket to show off most of her chest while her mind flooded with thoughts of teasing her favorite little squirrel tonight after not seeing him for so long. She giggled to herself softly as she zipped back up and headed out of the house.
Jenny smiled as the cold air outside nipped at her face, cooling her down as she heated up more and more from thinking about little Dexter as she walked to his house. She took a deep breath to calm herself as she made it to the young rodent's house, taking a moment to collect her thoughts before knocking on the door. She smiled warmly as the door opened, happy to see the woman on the other side. “Wow, you look gorgeous. Big date tonight?” the young husky asked as she stepped inside. 
Dexter's mother blushed lightly at the compliment, smiling and nodding. “Yes, first one in years. Thank you so much for coming tonight, I'm sorry I had to call you. I hope I didn't interrupt any plans.” she said as she walked towards the kitchen, motioning for Jenny to follow. “I ordered pizza a little bit ago so please, help yourself to anything if you're hungry. Dexter already ate, but there's ice cream in the freezer for later. He...had kind of a bad day today, so I ran to the store and got it for him after school.” she continued with a sadness in her voice.
“Oh no, what happened?” Jenny asked, concerned for the small boy. Just as the older squirrel opened her mouth to speak, an alarm on her phone went off.
She quickly pulled out her phone and tapped the screen, sighing anxiously as she turned off the alarm and slipped her phone back into her purse. “He asked a girl in his class to be his valentine and she turned him down pretty harshly. A couple other kids laughed at him and he was crying for a while. Poor kid. I didn't tell him you were coming tonight, he's expecting the normal sitter, but I'm hoping seeing you will make him feel at least a little better. He asks about you a lot. He asks when you're going to babysit next every time he sees you outside, it's really cute. I have to keep telling him you have school so that's why I haven't called you back since the first time, but then this date came up and it's the weekend so I figured I'd give it a shot. Thanks again for helping out, you're a genuine life saver. I have to go now or I'll be late, emergency numbers are on the fridge and I have you set to a special ringtone on my phone so I'll pick up if anything goes wrong.”
Jenny's heart soared hearing how Dexter always asked about her, unable to hide a slight blush forming on her cheeks even as she felt a sadness for what her favorite boy had gone through today. “Go on, we'll be fine. I promise. He was an absolute angel last time, I'm always happy to help. Good luck on your date, stay out as long as you need.” the young husky said with a wink, making the older squirrel struggle to hide her own blush. “Drive safe!” she shouted as the woman reached her car, quickly waving before she drove away.
Jenny set her stuff down next to the couch and quickly made her way to Dexter's room, standing outside his door and listening for a moment as she heard light sniffling from inside. She gently knocked and waited for a moment. “I-it's open.” the young squirrel said, followed by another sad sniffle. 
Jenny slowly opened the door and stepped inside, closing it behind her as she eyed the sad little boy watching cartoons on his TV, not even turning to see who was there. “Hey, Dexter. I heard you had a bad day.” she said softly, surprised at how quickly the young squirrel reacted to her voice.
“JENNY!” he shouted as he immediately jumped up and ran towards the husky standing in front of his door, quickly wrapping his arms around her and squeezing tight. “I missed you! I didn't know you were coming.” he said as the teen leaned down to hug him back.
They hugged each other tightly for a moment before Jenny pulled away and gently grabbed Dexter's cheeks, wiping her thumbs across the damp streaks under his eyes. “Well when I got a call to come watch my favorite squirrel I couldn't say no, could I? It's been a few months. I missed you too, Dex.” she said with a warm smile. She quickly leaned in a placed a small kiss on his nose before pulling away, smiling at the crimson blush shining through his light gray fur. “I heard you got turned down and laughed at today. Give me names, I'll go beat them up.” she said playfully, causing the young rodent to smile and giggle before he sniffled and wiped his eyes with his arm.
“Hehe, i-it's okay. I don't care about them anymore. Y-you're way cooler than her anyway. And prettier.” he said as he leaned forward to hug her again. Jenny's tail wagged as she felt her own face heating up at the unexpected compliment, wrapping her arms back around the small boy and placing a gentle kiss on top of his head. 
Dexter giggled bashfully at the kiss and squeezed tighter before pulling away. “Hehehe, my mom kisses my head like that, but I like it way more when you do it.” he said, his cheeks visibly red through his light gray fur. “I'm so happy you're here. You're the coolest and nicest babysitter I ever had. Do you want to watch cartoons with me? O-or something else, if you want. Or we can do-”
Jenny laughed cutely and cut the boy off, holding a finger to the boy's lips. “We can do whatever you want, big guy. I missed you a lot, too, and today's a special day.” she said as she stood and walked over to sit on the floor in front of his TV, patting the floor next to her with a smile. “C'mon, Dex. Whatever you want to watch.”
Dexter quickly ran to sit next to the husky, smiling and giggling as he picked up the remote to see what was on his favorite channel. “Hey, w-what did you mean today's a special day?” he asked as he set the remote back down, having found his favorite show on. 
“Well it's not every day a cute boy gets asked by his favorite babysitter to be her valentine.” she said with a sly wink. Dexter's cheeks burned hotly as he connected the dots in his head, his eyes going wide as he nodded and smiled. “Haha, I'm glad you said yes. That means you get the special valentine treatment tonight, and nobody can be sad about a bad day after Jenny's special valentine treatment.” she said as she leaned over to pick the boy up and set him between her legs to watch the TV together.
Dexter squeaked in surprise, flustered from being picked up by the older canine so easily, his ears twitching slightly as he felt the older girl's hand petting his head, her hand following the trail of his long, dark gray hair half way down his back before leaning forward and kissing him on the head again and gently stroking more. “W-what's the special valentine treatment?” he asked as he leaned his head into the hand gently petting it.
“Mmmm, the special valentine treatment is me pampering you all night, and we can do aaaaanything special you want. All you have to do is ask, big man.” she said before leaning her face down next to his ear and whispering “Anything at all.” placing a quick kiss on his cheek before pulling away and going back to petting him and running her fingers through his hair.
Dexter let out a contented sigh as he enjoyed the attention, his heart racing as he thought about what he wanted to do with his favorite babysitter tonight. His mind flashed back to her last visit over the summer, how nervous and unsure he was at first as the older girl molested him and took his virginity. A small bulge formed in his pants as he remembered the sensation of the older girls crotch swallowing his length and leaking her arousal against his waist. 
Dexter leaned his head back to rest on Jenny's chest, hissing slightly and jolting back up as he turned around to see what poked his head. “What's wrong, Dex?” Jenny asked as she watched the boy's eyes land on her chest.
“S-sorry, your zipper stabbed my head.” he said with a blush, rubbing the back of his head where it poked him. Jenny looked apologetic as she placed a hand on his cheek and gently rubbed it with her thumb.
“Well that's no good, I guess you'll just have to unzip me so it doesn't poke you again.” she said with a sly smile and a wink, making both their hearts race. Dexter reached towards the older teen's chest with a shaky hand, briefly struggling to grab hold of the small bit of metal before looking up to Jenny's eyes for reassurance. “Go on. it's okay, cutie. It's just a sweatshirt, it's not like I'm naked under there.” she continued, her face flushing as the young boy in front of her began to pull her zipper down, slowly revealing the soft, shaggy white fur of her chest.
Dexter watched in fascination as more of the older girl's fur was revealed, confused as he zipped down to the bottom of her chest and noticed still more fur, his heart racing as he realized she wasn't wearing anything underneath. He looked up again with wide eyes, mouth agape as he waited for Jenny to speak. “Oops, I guess I am naked under there. Silly me, haha.” she said with a wink as she motioned for him to keep going, the young boy quickly uncovering her the rest of the way.
Dexter gasped softly as the zipper came fully down and Jenny's hoodie parted, uncovering her stomach and chest as she leaned back to let the cloth slide off of her. The young squirrel's eyes were instantly drawn to her sparkly ruby bellybutton piercing on full display, his young mind flashing back again to the last time he'd seen the girl, his pants feeling much, much tighter all of a sudden. 
Jenny blushed as she watched the boy stare so intently at her, feeling her own arousal begin to soak into her pants as she leaned in and whispered “Anything you want, big guy.” into his ear as it gently twitched from her breath. She smiled as she watched him raise a hand and reach towards her belly, gently petting it. 
Dexter looked up as he heard Jenny sigh softly from the contact, her eyes lidded as she tilted her head back and enjoyed the feeling of her favorite little valentine exploring her body on his own. Dexter's little hands got more adventurous, both of them gently rubbing and scratching at her shaggy white belly fur, slowly moving their way up until Jenny moaned loudly from the young rodent's thumbs softly rubbing across her sensitive nipples. 
Jenny visibly shuddered and trembled, moaning as the little boy in front of her played with her rapidly hardening nubs, his hands easily cupping over the gentle swell of her nearly flat breasts. It had been so long since she got called to babysit, she'd forgotten how good it felt to let someone inexperienced learn their way around her body. She huffed and lifted her head back up, looking down at Dexter with pure adoration as he looked up to meet her gaze with his dark green eyes.
Jenny leaned forward and gently grabbed Dexter's face in both hands, rubbing his cheeks with her thumbs as she tilted his head up and kissed him. The young rodent's eyes widened in surprise, quickly closing them as he let himself go kissing her back, his little cock now throbbing uncomfortably hard in his pants as he reached full mast. 
Dexter let out a squeak of surprise when he felt Jenny's tongue swipe against his lips, his face burning even hotter than before as he got the hint and opened his mouth for the older canine. Jenny moaned into the younger boy's mouth as she licked at the inside of it, their tongues awkwardly wrestling together, emphasizing the small squirrel's inexperience and making Jenny all the more excited to help him practice. 
Jenny giggled softly as she moaned into their sloppy kiss, in love with the way Dexter's little tongue danced around with hers inside his mouth before pulling back to let them both catch their breath. “Do you remember what we did last time I was here, Dex?” she asked, breathing heavy as her heart pounded in her chest.
Dexter nodded, his mouth hanging open slightly as their mouths stayed connected by a thin strand of saliva slowly dripping down between them. “Did you like it?” she continued, smiling wide as he nodded again, his crimson cheeks burning clear through his light gray fur. “We can't do that again this time, but-” her heart sank at the instant look of devastation on the young squirrel's face. “BUT, we can do something I think you'll like even better. Would you like that?” 
Dexter nodded rapidly. “Yes! I-I mean, yes, please.” Jenny's face took on a playful smirk, leaning forward and pushing Dexter onto his back and crawling over him. She stared down at his blushing, nervous face and leaned down to kiss him again, one hand landing on his chest as she held herself over him with the other. The hand on his chest slowly rubbed and scratched its way down the small boy's body, pausing for a moment as it reached the bottom of his shirt before pulling it up to reveal the soft white fur of his belly. 
Dexter moaned and groaned into Jenny's kiss as she rubbed his stomach for a moment before reaching down lower and rubbing over the stiff little bulge in his gray sweatpants. Dexter's body stiffened from the contact with his crotch, briefly gasping in surprise from the feeling as his heart raced, worried it might pound straight out of his chest. 
Jenny pulled away from their kiss, Dexter's head moving up as his lips tried to meet with hers again, disappointed when he opened his eyes and saw she was too far away now. He smiled shyly as he watched her scoot down lower and lower towards his crotch, placing a small trail of kisses down his soft white belly. The young boy's mind raced anxiously as he watched the older girl's hands reach up for his waistband, gasping when she leaned in to place a kiss on the tip of his bulge before slowly pulling his pants down.
Dexter's heart pounded harder than ever in his chest as he watched Jenny hungrily eye his bulge, both of them gasping when his pants and underwear were pulled down far enough for his penis to spring upwards, his uncut little rod now fully exposed. Jenny smiled wide, her pants dampened with her own arousal as she leaned forward and nuzzled her nose into his tight little pouch, taking a deep whiff of his underaged balls. She moaned loudly as she memorized his scent, savoring the way it tickled her brain and made her salivate.
Dexter watched on in shock as the older girl's tongue left her mouth and swiped across his sack, gasping sharply as he thought about how wrong this was, how they probably shouldn't be doing this. He knew the games they played were naughty, but he'd enjoyed it so much last time that he simply didn't care enough to stop. He savored the feeling of losing his virginity to this beautiful canine, and was happy to finally be able to feel it again after so many months of trying and failing to come anywhere close to replicating the sensations he craved on his own. 
Jenny blushed hotly at the small gasps and sounds of pleasure leaving the young boy, enjoying the slight tremble shaking through his body as he let the older girl have her way with him. Jenny's wet canine tongue thoroughly slathered his tight little pouch, placing a big wet kiss at the top of his scrotum where it met the bottom of his shaft. She placed a long, slow, wet lick up his three inch twitching length, savoring his young taste and enjoying the feeling of his entire body stiffening as he gasped and moaned.
Dexter could no longer form words in his mind as he felt Jenny's skilled tongue reach the top of his penis and work its way down into his foreskin, slowly licking directly at his throbbing, sensitive pink tip. His little prick throbbed hard as Jenny's mouth finally dipped down and closed over it, sealing him inside of her hot, wet maw as she thoroughly ran her tongue around the inside of his foreskin before pursing her lips and bobbing her head down, rolling it back and exposing his bare head against her tongue. 
Jenny lowered her head all the way down, her nose pressing into the young rodent's pelvis as she slathered his underdeveloped cock in a long, loving wet kiss he would never forget. She moaned around his twitching length, her tongue sticking out of her mouth to lick at his tight little sack below while she lightly bobbed her head, swallowing his length whole as she pushed it against the roof of her mouth, making sure to pleasure every exposed spec of his throbbing penis. Her ears twitched with the sound of every overwhelmed gasp and moan leaving the cub's mouth, her pants utterly drenched in her arousal as she serviced the boy and refused to touch herself, focusing only on Dexter's pleasure despite her own hot, leaking need.
Dexter was lost in overwhelming pleasure as he savored the feeling of his babysitter's hot, wet tongue teasing across the folds of his rolled back foreskin, and rubbing directly against his sensitive pink tip as it throbbed and leaked small dribbles of pre cum into her mouth. He was no longer in control himself, giving up his body to his pleasure as he reached his hands forward and grasped her head, pushing her up and down as he felt that familiar pressure he craved so much slowly building in his pelvis. He savored the gasp Jenny released around his penis from the unexpected hands on her head, his hips beginning to buck all on their own in tandem with his hands shoving the older girl up and down on him.
Jenny salivated hard, enjoying the unmistakable flavor of young boy leaking out onto her tongue, lost in her own pleasure as she gave up control to the boy holding her head. She absolutely loved knowing she'd made her favorite boy feel so good he took control of his own pleasure, utterly lost in the bliss of letting the young boy have his way with her face. She gasped and moaned as his hips rapidly battered against her face, her tongue working double time to attempt to pleasure the young squirrel as much as possible.
“Jenny, h-haaaah, Jenny…” Dexter moaned out as the pressure in his pelvis reached the base of his little prick. “Jenny, p-please, h-aaaahnnnngh, JENNY! AAAAAAAHHHHN~” he screamed as searing hot pleasure shot up his throbbing young length and splattered thin, watery streams of barely pubescent semen against the back of the older girls throat, causing her to choke and gag briefly as her mouth was overwhelmed with the flavor of his underdeveloped young seed. She continued to lick and swirl her tongue around his oversensitive pink tip as much as she could, even as he held her head down firmly against his pelvis while he ejaculated for only the second time in his young life, directly inside of her mouth. 
Dexter's mind was entirely blank, fully overwhelmed by the intense stimulation on his throbbing little cock as he emptied his balls into his babysitter. He couldn't form words, let alone thoughts as he tightly gripped the older girl's head still while his body trembled as his orgasm slowly died down. Jenny's ears were splayed flat as she was lost in pleasure of her own. A surprise orgasm ran through her as she soaked her pants with hot slick need, overwhelmed with pleasure and joy just thinking about how good she was making Dexter feel.
Jenny continued to gently lick and suck the slowly softening penis in hour mouth until Dexter pulled her head up, hissing slightly from over stimulation. The older husky licked around inside her mouth to savor every bit of the boy's taste that she could, quickly placing one last gentle kiss on the tip of the boy's now fully softened length before leaning forward and placing another gentle kiss on his nose as he laid there panting, a strong feeling of comfort and relief flowing through his body as he came down from his intense orgasm. He giggled softly feeling Jenny's sweet little peck on his nose, his eyes opening slightly as he turned to face her, smiling happily as he sat up and wrapped his arms around her.
Jenny smiled and hugged back, feeling the little rodent begin to go limp in her arms, clearly tired from the overwhelming experience. “Did you like that, Dexter?” she asked softly, blushing as she felt him simply nod his head and squeeze her even tighter. “You tired, big guy?” she laughed as he shook his head no, even as his grip around her loosened and he began to slip away, his breathing slowing as he began to fall asleep in her arms. “You know your mom bought ice cream to make you feel better today, do you want some?” she asked.
“Mmmh, I don't need ice cream to feel better when I have you.” he said sleepily, comfy as can be in Jenny's arms. The husky's heart soared with adoration for the young boy as she smiled and squeezed him again, placing another kiss on his head as she scooped him up in her arms and placed him on his bed, laughing softly seeing how he'd fallen asleep before his head had even hit the pillow.
Jenny quietly left the room and made her way back to the couch to grab her bag, happy she always brought a change of clothes in case of emergencies as the wet pants sticking to her thighs got cold and uncomfortable. She carefully stepped back into Dexter's room, smiling as she saw him curled up and holding his big, fluffy tail like a body pillow. She quickly stripped out of her wet pants and underwear and slipped on a fresh pair of panties after wiping her thighs with the dry part of her dirty pants, slipping into the bed next to the boy.
The older husky slipped into the bed and scooted towards the young squirrel, surprised when he turned around to face her and wrap an arm around her. She smiled warmly as he nuzzled his head into her chest, rubbing his face around slightly as he got comfortable. She heard him mumble in his sleep when he got stopped moving, blushing hard when she heard him whisper “Mmmh, love Jenny.” under his breath before he went fully limp. 
Jenny wrapped an arm around the boy and squeezed him close, dipping her face down to kiss him on the head again. “I love you too, Dexter.” she whispered back as she closed her eyes and comfortably drifted off to sleep with him, a warm, loving smile on her face.